US6066761A - Method for isolating 3-[2-chloro-4-(trifluoromethyl)-phenoxy]-benzoic acid - Google Patents
Method for isolating 3-[2-chloro-4-(trifluoromethyl)-phenoxy]-benzoic acid Download PDFInfo
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- US6066761A US6066761A US09/355,277 US35527799A US6066761A US 6066761 A US6066761 A US 6066761A US 35527799 A US35527799 A US 35527799A US 6066761 A US6066761 A US 6066761A
- Authority
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- United States
- Prior art keywords
- acid
- organic
- trifluoromethyl
- chloro
- phenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 238000000034 method Methods 0.000 title claims abstract description 23
- ONKRUAQFUNKYAX-UHFFFAOYSA-N 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 ONKRUAQFUNKYAX-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000012074 organic phase Substances 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052751 metal Inorganic materials 0.000 claims abstract description 15
- 239000002184 metal Substances 0.000 claims abstract description 15
- 239000008346 aqueous phase Substances 0.000 claims abstract description 14
- 150000007524 organic acids Chemical class 0.000 claims abstract description 13
- 239000012071 phase Substances 0.000 claims abstract description 11
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 238000002955 isolation Methods 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 235000011054 acetic acid Nutrition 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- DHAHEVIQIYRFRG-UHFFFAOYSA-N Fluoroglycofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 DHAHEVIQIYRFRG-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- QNHCWLYFWBZVOM-UHFFFAOYSA-N benzoic acid;hydrate Chemical compound O.OC(=O)C1=CC=CC=C1 QNHCWLYFWBZVOM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005226 trifluoromethylbenzenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
Definitions
- the present invention relates to a process for the isolation of 3-[2-chloro-4-(trifluoromethyl)pehnoxy]benzoic acid of the formula I ##STR2## from an aqueous solution of its metal salt, which comprises a) reacting the metal salt of 3-[2-chloro-4-(trifluoromethyl)-phenoxy]benzoic acid with an organic or inorganic acid;
- 3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid of the formula I is an intermediate for the preparation of the herbicides acifluorfen, fluoroglycofen and lactofen, which are prepared in DE-A 23 11 638, EP-A 20 052, DE-A 30 29 728 and U.S. Pat. No. 4,031,131.
- the benzoic acid derivative of the formula I is precipitated from its salt solution in crystalline form by neutralization with an inorganic acid, isolated by filtration, washed with water and dried.
- the trifluoromethylbenzene derivative of the formula II is reacted with the dimetal salt of 3-hydroxybenzoic acid to give the metal salt IV of the benzoic acid derivative.
- the isolation of the free acid of the benzoic acid derivative of the general formula I is carried out in three steps.
- step a) the aqueous solution of the metal salt of the benzoic acid derivative of the formula I is reacted with an organic or inorganic acid.
- any monovalent or polyvalent metal salt Me + of the compound of the formula IV can be used as starting material. Preference is given to water-soluble metal salts.
- the alkali metal salts preference is given to the alkali metal salts. Particular preference is given to potassium and sodium salts.
- organic and inorganic acids are suitable for neutralizing the metal salts of the formula IV.
- suitable organic acids are formic acid, acetic acid, propionic acid and mixtures thereof. Preference is given to using acetic acid.
- Suitable inorganic acids are hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and mixtures thereof.
- the organic or inorganic acid is added to the aqueous solution of the metal salt of the formula IV with stirring at a temperature from 20 to 127° C., preferably 20 to 115° C., until a pH of less than 5, preferably less than 4.5, is obtained. This corresponds to approximately 1 to 6 times the molar amount of acid per mole of a metal salt of the formula IV, preferably 1 to 5 times the molar amount of acid. If the temperature is below about 90° C., the benzoic acid derivative I precipitates.
- step b) the reaction mixture is heated until the benzoic acid derivative I is molten and a liquid two-phase system of organic phase and aqueous phase has formed.
- the lower organic phase contains the molten benzoic acid derivative I.
- the temperatures in step b) are from 90 to 127° C., preferably from 95 to 115° C.
- steps a) and b) in a single reaction step by carrying out the addition of the acid at a temperature from 90 to 127° C., preferably from 95 to 115° C. If the reaction is carried out in this way, a liquid two-phase system which separates into a lower organic phase and an upper aqueous phase is formed directly.
- step c) the organic phase is separated from the aqueous phase.
- the organic phase comprises the benzoic acid derivative, water and, if used, organic acid.
- the organic phase can be used directly for further processing.
- the organic phase may be dewatered in step d) prior to further processing.
- the dewatering is carried out by distilling off the water and remaining organic acid. If acetic acid is used as organic acid in the neutralization step a), the water may also be removed by distilling off some or all of the acetic acid.
- the process according to the invention can be carried out continuously and batchwise, and at atmospheric pressure, superatomospheric pressure and reduced pressure.
- the yield of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid in the organic phase is very high.
- the aqueous phase which has been removed contains less than 3%, preferably less than 2%, of this compound.
- the phases separate; the lower brown organic melt phase weights, after the aqueous phase has been removed, 594 parts and contains in addition to 84.0 parts of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid 12.9 parts of water and 2.33 parts of acetate as free acid or as potassium slat.
- the aqueous phase only contains ⁇ 0.1% of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid.
- the phases separate; the lower brown organic melt phase weights, after the aqueous phase has been removed, 485 parts and contains in addition to 82.5% by weight of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid 14.5% by weight of water and 2.5% by weight of acetate as free acid or as sodium salt.
- the aqueous phase only contains ⁇ 0.1% of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the isolation of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid of the formula I ##STR1## from an aqueous solution of its metal salt comprises a) reacting the metal salt of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid with an organic or inorganic acid;
b) heating the reaction mixture until a liquid two-phase system of organic and aqueous phase has formed; and
c) separating the organic phase from the aqueous phase.
Description
This application is a 371 of PCT/EP98/00705 filed Feb. 9, 1998.
The present invention relates to a process for the isolation of 3-[2-chloro-4-(trifluoromethyl)pehnoxy]benzoic acid of the formula I ##STR2## from an aqueous solution of its metal salt, which comprises a) reacting the metal salt of 3-[2-chloro-4-(trifluoromethyl)-phenoxy]benzoic acid with an organic or inorganic acid;
b) heating the reaction mixture until a liquid two-phase system of organic and aqueous phase has formed; and
c) separating the organic phase from the aqueous phase.
3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid of the formula I is an intermediate for the preparation of the herbicides acifluorfen, fluoroglycofen and lactofen, which are prepared in DE-A 23 11 638, EP-A 20 052, DE-A 30 29 728 and U.S. Pat. No. 4,031,131.
According to U.S. Pat. No. 4,031,131, the benzoic acid derivative of the formula I is precipitated from its salt solution in crystalline form by neutralization with an inorganic acid, isolated by filtration, washed with water and dried.
This process has a number of disadvantages: the handling of solids leads to the formation of crusts during the crystallization, causing the crystals to absorb significantly more water. During drying, this leads to clogging and to bottlenecks in the process.
It is an object of the present invention to provide a process for the isolation of the benzoic acid derivative of the formula I which does not have these disadvantages.
We have found that this object is achieved by the process described at the outset.
In U.S. Pat. No. 4,031,131, the preparation of the benzoic acid derivative of the formula I is carried out according to the following scheme: ##STR3##
The trifluoromethylbenzene derivative of the formula II is reacted with the dimetal salt of 3-hydroxybenzoic acid to give the metal salt IV of the benzoic acid derivative.
In the process according to the invention, the isolation of the free acid of the benzoic acid derivative of the general formula I is carried out in three steps.
In step a), the aqueous solution of the metal salt of the benzoic acid derivative of the formula I is reacted with an organic or inorganic acid.
In principle, any monovalent or polyvalent metal salt Me+ of the compound of the formula IV can be used as starting material. Preference is given to water-soluble metal salts.
Among the water-soluble metal salts, preference is given to the alkali metal salts. Particular preference is given to potassium and sodium salts.
All organic and inorganic acids are suitable for neutralizing the metal salts of the formula IV. Examples of suitable organic acids are formic acid, acetic acid, propionic acid and mixtures thereof. Preference is given to using acetic acid.
Suitable inorganic acids are hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and mixtures thereof.
The organic or inorganic acid is added to the aqueous solution of the metal salt of the formula IV with stirring at a temperature from 20 to 127° C., preferably 20 to 115° C., until a pH of less than 5, preferably less than 4.5, is obtained. This corresponds to approximately 1 to 6 times the molar amount of acid per mole of a metal salt of the formula IV, preferably 1 to 5 times the molar amount of acid. If the temperature is below about 90° C., the benzoic acid derivative I precipitates.
In step b) the reaction mixture is heated until the benzoic acid derivative I is molten and a liquid two-phase system of organic phase and aqueous phase has formed. The lower organic phase contains the molten benzoic acid derivative I. The temperatures in step b) are from 90 to 127° C., preferably from 95 to 115° C.
It is also possible to carry out steps a) and b) in a single reaction step by carrying out the addition of the acid at a temperature from 90 to 127° C., preferably from 95 to 115° C. If the reaction is carried out in this way, a liquid two-phase system which separates into a lower organic phase and an upper aqueous phase is formed directly.
In step c), the organic phase is separated from the aqueous phase. The organic phase comprises the benzoic acid derivative, water and, if used, organic acid.
The organic phase can be used directly for further processing.
However, the organic phase may be dewatered in step d) prior to further processing. The dewatering is carried out by distilling off the water and remaining organic acid. If acetic acid is used as organic acid in the neutralization step a), the water may also be removed by distilling off some or all of the acetic acid.
The process according to the invention can be carried out continuously and batchwise, and at atmospheric pressure, superatomospheric pressure and reduced pressure.
In the process according to the invention, the yield of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid in the organic phase is very high. The aqueous phase which has been removed contains less than 3%, preferably less than 2%, of this compound.
In this isolation process, the handling of solids is dispensed with and the dewatered melt of the 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid can be employed directly for preparing acifluorfen, 5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoic acid, by nitration.
2500 parts of a 20% strength solution (by weight, based on the free acid) of the potassium salt of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid (1.58 mol) of pH 8.8 in a stirred heatable 3 liter glass vessel are diluted with 498 parts of water and heated to 50° C. At this temperature, 370 parts (6.17 mol) of acetic acid are then added within 90 minutes with stirring, causing the 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid to precipitate. The pH of the resulting suspension is 4.3. The suspension is then heated to 96° at which the solid melts and a two-phase liquid mixture is formed. After the stirrer has been switched off, the phases separate; the lower brown organic melt phase weights, after the aqueous phase has been removed, 594 parts and contains in addition to 84.0 parts of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid 12.9 parts of water and 2.33 parts of acetate as free acid or as potassium slat. The aqueous phase only contains <0.1% of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid.
2500 parts of a 20% strength solution (by weight, based on the free acid) of the sodium salt of 3-([2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid (1.58 mol) of pH 8.8 in a stirred heatable 3 liter glass vessel are diluted with 498 parts of water and heated to 50° C. At this temperature, 360 parts (6.0 mol) of acetic acid are then added within 90 minutes with stirring, causing the 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid to precipitate. The pH of the resulting suspension is 4.3. The suspension is then heated to 100° C. at which the solid melts and a two-phase liquid mixture is formed. After the stirrer has been switched off, the phases separate; the lower brown organic melt phase weights, after the aqueous phase has been removed, 485 parts and contains in addition to 82.5% by weight of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid 14.5% by weight of water and 2.5% by weight of acetate as free acid or as sodium salt. The aqueous phase only contains <0.1% of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid.
Claims (12)
1. A process for the isolation of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid of the formula I ##STR4## from an aqueous solution of its metal salt, which comprises a) reacting the metal salt of 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid with an organic or inorganic acid;
b) heating the reaction mixture until a liquid two-phase system of organic and aqueous phase has formed; and
c) separating the organic phase from the aqueous phase.
2. The process as claimed in claim 1, wherein steps a) and b) are combined in one reaction step.
3. The process as claimed in claim 1, wherein the organic phase of step c) is dewatered in an additional step d).
4. The process as claimed in claim 1, wherein the metal salt used is a sodium or potassium salt.
5. The process as claimed in claim 1, wherein the organic acid used is formic acid, acetic acid, propionic acid or mixtures thereof.
6. The process as claimed in claim 5, wherein the organic acid used is acetic acid.
7. The process as claimed in claim 1, wherein the inorganic acid used is hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid or mixtures thereof.
8. The process as claimed in claim 1, wherein sufficient organic or inorganic acid is added in step a) to obtain a pH of less than 5.
9. The process as claimed in claim 1, wherein the reaction mixture in step b) is heated to at least 90° C.
10. The process as claimed in claim 9, wherein the reaction mixture is heated to at least 96° C.
11. The process as claimed in claim 3, wherein the organic phase is dewatered in step d) by distilling off the water.
12. The process as claimed in claim 6, wherein the organic phase of step c) is dewatered in an additional step d) by distilling off acetic acid.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19706875 | 1997-02-21 | ||
| DE19706875 | 1997-02-21 | ||
| PCT/EP1998/000705 WO1998037054A1 (en) | 1997-02-21 | 1998-02-09 | Method for isolating 3-[2-chloro-4-(trifluoromethyl)-phenoxy]-benzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US6066761A true US6066761A (en) | 2000-05-23 |
Family
ID=7821033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/355,277 Expired - Fee Related US6066761A (en) | 1997-02-21 | 1998-02-09 | Method for isolating 3-[2-chloro-4-(trifluoromethyl)-phenoxy]-benzoic acid |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6066761A (en) |
| EP (1) | EP0968169B1 (en) |
| JP (1) | JP2001512467A (en) |
| KR (1) | KR20000075491A (en) |
| CN (1) | CN1248239A (en) |
| AR (1) | AR011844A1 (en) |
| AT (1) | ATE217860T1 (en) |
| AU (1) | AU744848B2 (en) |
| BR (1) | BR9807583A (en) |
| CA (1) | CA2281828A1 (en) |
| DE (1) | DE59804199D1 (en) |
| HU (1) | HUP0000916A3 (en) |
| PL (1) | PL335406A1 (en) |
| RU (1) | RU2173678C2 (en) |
| WO (1) | WO1998037054A1 (en) |
| ZA (1) | ZA981418B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6096889A (en) * | 1999-06-01 | 2000-08-01 | Basf Corporation | Process for making high performance dyes |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4031131A (en) * | 1975-09-29 | 1977-06-21 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
| US4076741A (en) * | 1972-03-14 | 1978-02-28 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| EP0020052A1 (en) * | 1979-05-16 | 1980-12-10 | Rohm And Haas Company | Novel substituted nitrodiphenyl ethers, herbicidal compositions containing them, processes for the preparation thereof and the use thereof for combating weeds |
| US4400530A (en) * | 1980-06-27 | 1983-08-23 | Ppg Industries, Inc. | Process for preparing substituted diphenyl ethers |
-
1998
- 1998-02-09 CA CA002281828A patent/CA2281828A1/en not_active Abandoned
- 1998-02-09 BR BR9807583A patent/BR9807583A/en not_active IP Right Cessation
- 1998-02-09 EP EP98906939A patent/EP0968169B1/en not_active Expired - Lifetime
- 1998-02-09 DE DE59804199T patent/DE59804199D1/en not_active Expired - Lifetime
- 1998-02-09 JP JP53620998A patent/JP2001512467A/en active Pending
- 1998-02-09 AT AT98906939T patent/ATE217860T1/en not_active IP Right Cessation
- 1998-02-09 HU HU0000916A patent/HUP0000916A3/en unknown
- 1998-02-09 AU AU62962/98A patent/AU744848B2/en not_active Ceased
- 1998-02-09 RU RU99119897/04A patent/RU2173678C2/en not_active IP Right Cessation
- 1998-02-09 WO PCT/EP1998/000705 patent/WO1998037054A1/en not_active Application Discontinuation
- 1998-02-09 CN CN98802652A patent/CN1248239A/en active Pending
- 1998-02-09 KR KR1019997007550A patent/KR20000075491A/en not_active Application Discontinuation
- 1998-02-09 PL PL98335406A patent/PL335406A1/en unknown
- 1998-02-09 US US09/355,277 patent/US6066761A/en not_active Expired - Fee Related
- 1998-02-20 AR ARP980100783A patent/AR011844A1/en not_active Application Discontinuation
- 1998-02-20 ZA ZA9801418A patent/ZA981418B/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4076741A (en) * | 1972-03-14 | 1978-02-28 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4-nitrodiphenyl ethers |
| US4031131A (en) * | 1975-09-29 | 1977-06-21 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
| EP0020052A1 (en) * | 1979-05-16 | 1980-12-10 | Rohm And Haas Company | Novel substituted nitrodiphenyl ethers, herbicidal compositions containing them, processes for the preparation thereof and the use thereof for combating weeds |
| US4400530A (en) * | 1980-06-27 | 1983-08-23 | Ppg Industries, Inc. | Process for preparing substituted diphenyl ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA981418B (en) | 1999-08-20 |
| CA2281828A1 (en) | 1998-08-27 |
| PL335406A1 (en) | 2000-04-25 |
| HUP0000916A3 (en) | 2001-02-28 |
| EP0968169B1 (en) | 2002-05-22 |
| EP0968169A1 (en) | 2000-01-05 |
| AU6296298A (en) | 1998-09-09 |
| JP2001512467A (en) | 2001-08-21 |
| ATE217860T1 (en) | 2002-06-15 |
| AR011844A1 (en) | 2000-09-13 |
| BR9807583A (en) | 2000-03-21 |
| CN1248239A (en) | 2000-03-22 |
| RU2173678C2 (en) | 2001-09-20 |
| HUP0000916A2 (en) | 2000-08-28 |
| DE59804199D1 (en) | 2002-06-27 |
| KR20000075491A (en) | 2000-12-15 |
| WO1998037054A1 (en) | 1998-08-27 |
| AU744848B2 (en) | 2002-03-07 |
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